Gilmore Girls: The lead male characters on the show, ranked worst to least awful

It has officially been 20 years since Gilmore Girls first aired, welcoming viewers into the cozy, kooky town of Stars Hollow – and the equally kooky lives of Lorelai and Rory Gilmore.

As its name would suggest, Gilmore Girls was a female-centric show, focusing primarily on the mother-daughter relationship at its heart, and giving prominence to great friendships like Rory and Lane, or Lorelai and Sookie.

Still, there were some important men in Rory and Lorelai’s lives, too. Some were love interests, others were relatives, employees, or random Stars Hollow-ites. Some were good and some were bad. To mark the show’s anniversary, we’ve taken a closer look at exactly who was bad and who was good, and in which measure.

15. Straub Hayden

Straub – Christopher's father – was so horrible it strained credibility. I mean, really, who shows such open disdain for his own granddaughter? The greatest tragedy of Straub’s life was that Christopher did not go to Princeton, the family Ivy League – and he blamed Lorelai, more so than Christopher himself, for it. To quote Emily Gilmore, Straub was a “big a**”.

14. Logan Huntzberger

Logan usually gets the most flack for being a bad influence on Rory – and that’s not entirely wrong. His biggest issue – and the one at the heart of most of his unpleasantness – was his difficult relationship with his parents, but that excuse was bound to get tired over time. Typical Logan behaviour: when Rory confronted him over talking to a bartender “like a servant”, his immediate response was: “Well…” And then: “The fact that this is a free country means that I can speak to anyone in any manner which I choose.” Ugh. In the words of Paris: “You, Logan Huntzburger, are nothing but a two-bit, spoiled waste of a trust fund! You offer nothing to women or the world in general! If you were to disappear from the face of the earth tomorrow, the only person that would miss you is your Porsche dealer!” We love Paris.

13. Christopher Hayden

Does anyone actually like Christopher? His parents treated Lorelai appallingly for getting pregnant, ignoring the fact that Christopher did actually have some involvement. And Christopher never stood up for her, either. He left Lorelai’s life at several key moments and came back periodically, only to mess up her life all over again.

12. Tristan Dugray

Yes, Tristan showed a softer side every once in a while, but overall he was a spoiled brat who thought for a long time that the best way to show his affection for Rory was to pick on her. And even after that, his romantic indecision threatened Paris and Rory’s friendship on more than one occasion. Boo, Tristan. Although we did feel slightly sorry for him when he got packed off to military school. 

11. Dean Forester

Dean started off sweet. He was the ultimate first love, the sweet high-school boyfriend who, to his credit, completely went along with Rory and Lorelai’s life rules (“Go with their bits – like if you’re eating pizza with them and Lorelai decides that the pepperoni is angry at the mushrooms because the mushrooms have an attitude, and then she holds up a pepperoni and the pepperoni asks for your opinion? Don’t just laugh. Answer the pepperoni.”) Then, he grew judgmental, kind of controlling, and of course, he cheated on his new wife with Rory. Bye, Dean.  

10. Zack Van Gerbig

Zack got Lane pregnant during their honeymoon, resulting in the most universally hated plotline on Gilmore Girls: Lane’s pregnancy with twins and, by extension, the fact that the show ended with her having to put her rock star dreams on hold. Oh, and the fact that this incident put her off sex for life. On a different note, Zack’s jealousy and emotional immaturity was what caused the band to split the first time round. It felt like Lane could have done better.

9. Henry Cho

Henry went out of his way to foster a secret relationship with Lane after meeting her at a party. In the end, it was not to be, but there are no real complaints against Henry. He’s just that first boyfriend with whom you can’t really make things work.

8. Richard Gilmore

Richard, Richard, Richard. He was at times so problematic, and at other times so cool. On the surface, he was a stuck-up, old-fashioned, controlling, sometimes cold patriarch. But there was something so genuine and so sincere in the ways he tried to connect with Rory. He believed in her potential and fostered her curiosity about the world. He weren’t always the best father to Lorelai, but then again he almost got into a fist-fight with Straub Hayden when he insulted her. He was a Grade-A snob, and that sometimes got in the way of his personal relationships – including Rory and Lorelai’s boyfriends – but he generally tried to do what was best for his family.

7. Michel Gerard

Quick on his feet, sardonic but not cruel, Michel was in his own, reluctant way, the glue that held the Independence Inn together. He was nothing if not honest (sometimes slightly too honest), and he had a healthy sense, shall we say, of personal boundaries. 

6. Kirk Gleason

Kirk was Stars Hollow’s lovable weirdo. Was he sometimes irritating? Yes. Was he almost always odd? Yes. But he lived life on his own terms, unapologetically so, and never hurt anyone in the process (at least not majorly). No real complaints here.

5. Jackson Belleville

When he wasn’t busy bickering with Sookie about produce, Jackson was one of the sweetest guys in Stars Hollow. He did lie to his wife about getting a vasectomy, which many fans complained was completely out of character, not to mention one of the most bizarre storylines in Gilmore Girls. Asides from that issue, which we’ll chalk up to a bonkers decision on the writers’ part, Jackson was a good, supportive partner to Sookie and an all-around nice person.

4. Luke Danes

Gilmore Girls wanted us to pine for Luke a little more than strictly necessary. He grew more open and more emotionally vulnerable as the show went on – and became the perfect partner for Lorelai. Earlier on, though, he was  gruff and guarded. That was supposed to be part of his charm, but… “emotionally stunted” always loses you points on the dreamboat scale. Nonetheless, he showed up for Lorelai when she needed him, and he served as a father figure of sorts for both Rory and his nephew Jess (a tiny bit weird, since Jess and Rory dated). 

3. Max Medina

Max was pretty great. Sure, there was the whole “dating his student’s mother” aspect, but all the men on Gilmore Girls were pretty flawed. Max was kind, intelligent, devoted to both Lorelai and Rory, and ready to commit to a relationship – at times a little too much so. Ultimately, though, he was a little too boring and straight-edge to fit into the quirky world of the Gilmore Girls.

2. Dave Rygalski

Gilmore Girls fans will never forgive California for taking Dave away from Lane, ending their perfect relationship. Of course, their love was young, but it would have been nice to see them reconnect later on. Dave was the sweet music-loving partner Lane deserved. And his historic monologue (“I don’t smoke. I don’t drink. I’ve never gotten a ticket. I’m healthy. I take care of myself. I floss. ...I never play video games in case they do someday prove that playing them can turn you into a serial killer. I don’t drink coffee. I hate soda because the carbonation freaks me out. I’m happy to give up meat if you feel strongly about it. I don’t mind wearing a tie.”) convinced Mrs Kim to let her take Lane to the prom. And he read the entire Bible in one night in the name of love!

1. Jess Mariano

Aaaah, Jess. The dreamy, bookish, rebellious Jess. Aside from the obvious bad boy appeal, Jess had an authentic connection with Rory. They bonded over books, the closest thing to Rory’s heart. And yes, Jess had a lot of growing up to do, so that relationship got messy at times. But he got Rory’s references, believed in her potential, respected her as a person… and made her laugh. These two were good together. There was room in their relationship for their respective imperfections as well as room for growth – and chemistry galore.